Red's Bedtime Stories
by redisthenewblackington
Summary: At night, Liz gets to learn more about Red's past through a series of autobiographical bedtime stories. Lizzington.
1. Chapter 1

Author's Note: This is an idea that jumped into my head and refused to be ignored. Each chapter will consist of a little bedroom chatter between Red and Liz, and then a few short bedtime stories. Who doesn't love Red's stories? Some of them will be entirely fabricated by me, and others will build upon Red's canon anecdotes.

I'm giving this a T rating, but it might be a little closer to a tame M, at times. A lot of the banter is sexual in nature, but doesn't describe any sexual activities in detail.

In a lot of ways, this will probably read like a series of unconnected one-shot crack!Fics.

Thanks for reading, and please let me know what you think! If you have any bedtime story requests, feel free to ask, and I'll try to make it happen.

Disclaimer: I own nothing and earn nothing.

-...-...-...-...-...-

 **Prologue**

After working together for three years, dancing around each other, teasing and tempting, Raymond Reddington and Elizabeth Keen had finally given in to their desire for one another. Unfortunately, the better Liz came to know Red, the more she wanted to know, and he still had an untold number of secrets that he couldn't share.

One night, after making love, she accidentally stumbled upon an idea that gave her an opportunity to look into his past, on his own terms. Red, usually fearful of the banality of routine, happily jumped right into this one.

-...-...-...-...-...-

 **Chapter One**

"I can't sleep," Liz whined.

Red kissed a line from her shoulder up to her ear and whispered, "You wanna go again?"

"Yes, but..." This was a little embarrassing - a problem that frankly, she'd never had before.

"But?"

"It's just that we've been... and you're so..." She sighed. "I'm more than a little sore. My ladybits are waving a white flag."

"Oh... Message received." He briefly met her eyes, licked his lips, and ducked beneath the covers.

"Red!" When her hand found its way to the back of his head, he was surprised to feel her pulling him up, rather than pushing him down.

"I apologize, sweetheart. You'll have to be a little more direct with me here, because I absolutely cannot get enough."

"I promise to work on that. It's just, with Tom, I nev-"

"Lizzie?" He interrupted, "Can we just officially state that I'm superior to him in all sexual endeavors, and then never bring it up again?"

"Hmm... I'm a little surprised that such an oversized ego would need to be stroked."

"Only in the shower, when I'm away on business," he deadpanned.

"Let's just try to sleep again."

Red pulled her into his arms and kissed the corner of her mouth. "As you wish. Goodnight."

Twenty minutes later, Liz was still wide awake. "Red?" She softly whispered, not wanting to wake him if he'd fallen asleep.

"Lizzie."

"Tell me a story."

"Ouch. My stories are so boring that they put you to sleep?"

"I love your stories. If I didn't love them, I wouldn't have asked. But your voice... it sort of makes me melt, and if I melt enough, I just might fall asleep."

"Good answer. Do you want an autobiographical story?"

"Yes."

"About what?"

"Tell me a story about... hmm... getting in trouble at school - whatever incidents spring to mind first."

He chuckled. "Oh, this could take all night."

"You say that every night."

-...-...-...-...-...-

 _In kindergarten, we had nap time for thirty minutes every day. As you know, I've never been very good at naps, or at sleep in general, unless I'm exceptionally exhausted. So for me, nap time was extraordinarily long and boring. I'd keep my eyes closed and try my damnedest to be still. It was a torturous battle for self control._

 _One day, however, I opened my eyes and found that, much to my delight, I wasn't being watched. The teacher faced away from the classroom, writing a list of vocabulary words on the chalk board. Now, I didn't actually do anything bad that day, but I did begin to ponder how to best exploit that minuscule moment of nap time freedom._

 _Allow me to insert a disclaimer here. My creativity was far from developed at that age, so my chosen act of rebellion wasn't particularly original._

 _I decided to free the class pet, a bird named Charlie. In my head, I imagined tiptoeing over, soundlessly opening the cage, and then returning to my cot to wait for all hell to break loose after the bird flew out._

 _As I'm sure you've already predicted, it didn't go that well. I did make it to the cage, but when I tried to open it, the metal latch cut through the silence with a horrible screech. My teacher whipped around and scowled so hard that the mere memory still makes me tremble in fear._

 _But the bird stayed in the cage._

 _Turns out that due to an old injury, he couldn't fly, anyway. For that little stunt, I had to stay inside and clean the classroom while everyone else went outside for recess. In that, I found yet another opportunity to entertain myself during nap time. I asked if I could clean up and put away the toys while everyone else napped every day. Imagine that - a little boy asking for permission to clean. That's how much I hated nap time. Of course, my teacher assumed that I had some kind of nefarious motive, so she denied my request_.

-...-...-...-...-...-

Liz offered a sympathetic smile. "It sounds like you've always been a little misunderstood."

"Maybe," Red replied, gently combing his fingers through her hair.

"A bird is a ridiculous classroom pet, anyway, regardless of its inability to fly."

"It is, isn't it? Would you like to hear another?"

"Yes, please."

-...-...-...-...-...-

 _Like most military families, my household was very strict. For that reason, while I was at school, I got into a lot of the not-so-good things that other kids probably did at home. That includes smoking._

 _In fifth grade, I had a friend named Marnie Peterson. My best friend, really. Funny little bat-faced girl. I adored her!_

 _She often complained about how her dad always smoked cigars, and I didn't really understand why it bothered her so much. She said that she just hated the smell. Naturally, I suggested that she steal one so that we could give it a try. I wanted to find out for myself._

 _Since she brought the cigar, I took care of the matches. During lunch time, we slipped out through the back door and ran down to the woods. I don't think we smoked even a quarter of it before we decided to just bury the rest and go back._

 _I almost got away with it. We made it back before anyone had even noticed that we were gone, but at some point - and I don't remember when or exactly how - our teacher smelled it on me. Not Marnie, though. Just me. I must have been standing downwind._

 _She sent me to the pricipal's office, and ohhh, I got grilled pretty hard. He wanted to know where I got it, where I smoked it, why I did it. On and on. I rocked shut, tight as a clam. He said he'd go light on my punishment if I answered his questions, but I refused to tell him anything._

 _Good idea? Bad idea? I don't know. He'd have to call my folks regardless, and their punishment was the only one that mattered to me. I don't even remember what the school did, but my dad took away my bike and my vinyl collection for a month._

-...-...-...-...-...-

"So, did you enjoy the cigar? Did trying it bring you any closer to understanding why Marnie hated them?"

"Not quite, and not at all. I found the smell appealing."

"Cigar smoke by itself isn't so great, but paired with the ineffable scent of man, ah... heaven. I wish you could see how sexy you look with a cigar."

"Should I smoke them around you more often? You must feel enormously conflicted about that - getting turned on by something that could kill me."

"Well gee, thanks. I wasn't thinking about it in those terms. There is something I've been dying to know, though... Do you sexy-smoke them on purpose? Are you trying to turn cigar-smoking into a sexual obscenity?"

Red smirked, waggling his eyebrows. "That depends. Which answer would you find more arousing?"

"Good question... I'm not sure, really."

He shrugged his shoulders. "Then neither am I."

"Not fair! You suck."

"Nuh uh. You do."

She smirked. "Not if you don't give me an answer."

Red dramatically put both hands over his heart. "Oh darling, that is a cruel joke. After experiencing the mind-blowing pleasure of your mouth, the idea that it'll never happen again... I just can't."

"So? Accidental sexual cigar gravitas or not?"

"Oh, fine. Mostly accidental. People tend to be a little more sexy when they're doing something they enjoy - something they want to savor. But I do, from time to time, find a little pleasure in exaggerating the motions. It satisfies my inner exhibitionist in a way that won't get me arrested."

"Gotcha."

"So... another?"

"Please and thank you."

-...-...-...-...-...-...-

 _This one is a little more tame, but I remember it well nonetheless because it earned me a lot of unexpected notoriety._

 _I began ninth grade in a brand-new, three-story highschool. The main stairwell had a wide-open layout. From the top of the stairs, on the third floor, you could look down and see all the people walking around the lobby on the first._

 _On day one, rather than immediately searching for our homeroom like everyone else, Carter Randall and I went up to the third floor to lean over the railing and try to see down the blouses of the girls walking through the lobby below. The novelty of being able to do so wore off in about eh... ten seconds, so Carter offered me five bucks to spit over the railing._

 _I figured that with the risk of getting caught rather high, five wasn't enough, so I persuaded him to double it. I tried to wait for the right time, when I had enough open space below not to hit anyone. Unfortunately, right after the spit left my lips, Maxine Avery came out of nowhere, sprinting right into the line of fire, unbeknownst to her._

 _She looked up in horror and screamed. At that point, if I'd only ducked or run away, I probably could have gotten away with it. Instead, I felt terrible, so I rushed down to apologize to her. Right then and there, less than ten minutes after walking through the door, I became known as the first person to get written up in the new highschool, for spitting on the most beautiful, popular girl there. To this day, I've never seen such an angry cheerleader._

 _But it's so funny... I'm standing there, apologizing, and she's just screaming at me, getting all flushed in the cheeks... and while this was happening, and everyone around us was staring, I fell in love with her a little._

 _Two months later, I became known as the guy who spit on the most popular girl in school, only to later convince her to be my date for the homecoming dance. In case you're wondering, yes, we were crowned king and queen._

-...-...-...-...-...-

"I feel like I say this a lot, but only you, Red. Only you could get away with something like that."

"Well, I did get in trouble."

"Yeah, but you know what I mean."

"And to think, forty years later, I was on the FBI's Most Wanted list, and managed to convince their most beautiful special agent to accompany me to a dance at the Syrian embassy."

Liz huffed a laugh. "Like I said, only you."


	2. Chapter 2

AN: In the second of the three stories in this chapter, the sexytalk goes up a little more. It isn't quite M material, but seemed worthy of mention just in case. Thanks for reading and reviewing!

Disclaimer: Nothing owned, all things borrowed.

-...-...-...-...-...-

The following night, they stayed in an enormous old mansion on the Chesapeake Bay. As soon as they went upstairs to the master suite, Liz ripped off Red's clothes and made up for a particular comment that she'd made the night before.

He was still panting when she climbed out of his lap and donned a silk robe that left very little to the imagination. "Would you like to go outside on the balcony and split a bottle of red?"

"You wish you could bottle me."

"Who wouldn't?" She smirked. "I feel like a cabernet. Napa Valley or Virginia?"

"Let's go local."

"Okay. I'll be right back."

A few minutes later, Liz returned from the kitchen with the bottle, corkscrew, two glasses, and a surprise hidden in her cleavage. With a jerk of her chin, she beckoned Red to follow her outside.

They each took a seat on the cedar porch swing, and Liz wedged the bottle between her thighs to open it, but Red reached for it, wordlessly offering to take care of it for her. "Nope!" She swatted his hand away and turned towards him, leaning forward so he could see into her robe. Red laughed, grinning from ear to ear. "Go ahead."

He lowered his head and used his teeth to pluck the cigar from her cleavage and quipped, "Dare I ask where you've hidden the matches?"

Liz blushed. "They're in my pocket, you letch."

After Red's cigar was lit and both were contentedly sipping their wine, she asked, "Mind telling me another bedtime story tonight?"

"Now?"

"Yes, please. Your stories from last night got me thinking... no one moves up through the ranks as quickly as you did after getting in trouble all the time in school. And if I know you, for every time you got caught, you must have gotten away with at least ten other misdeeds."

"I'm reticent to put a number on it, but yes, that's a fair assessment."

"So, tell me about the things you did that you were sure you'd be caught doing, but weren't."

"May I include stories that involve girls? Most of the better ones do."

"No holds barred. Anything goes."

-...-...-...-...-...-

 _In eighth grade, we had a field trip to the Baltimore Aquarium. If you ever had a chance to go while you lived there, then I hope that you took it. Without question, it's the very best thing that the city has to offer. Lovely place._

 _Since it was a two-hour drive from our school to the aquarium, we had to be driven to school early by our parents instead of taking the bus. My girlfriend at the time, Jocelyn Bishop, had just scored some excellent, fluffy buds with all these little red hairs in them. It had a ridiculous name that I'm guessing her dealer thought of so he could jack up the price. Pineapple Snapdragon, I think._

 _So anyway, she decided that we should get our parents to drop us off even earlier than necessary, so we could smoke up in the woods before heading inside for the roll call. And oh god... we were so baked. I think we almost got lost trying to find our classroom. My eyes were tiny slits. Couldn't have opened them normally to save my life._

 _But somehow, no one seemed to notice, and I think Josie and I just giggled the entire way to the aquarium. When we got there, we expected to be corralled from exhibit to exhibit, but they just handed out worksheets and turned us loose with a time and location to meet up again, for a dolphin show._

 _We had a blast, but within about an hour, we were just dragging our bodies around. I remember, we were checking out these enormous stingrays when Josie turned to me and said that she had another joint in her pocket. So like any foolishly cocky teenagers, we assumed that we could just go into the ladies room and smoke it, and no one would ever know._

 _She went in first to make sure it was empty, and then came out and grabbed me. Suddenly we're crammed together in this tiny stall, blazing down a fat joint, and a woman comes in to change her baby's diaper. We didn't know what to do. The bathroom was full of smoke, but we'd only smoked half of the joint. I wanted to flush it and run. She wanted to finish it. Three feet away, the poor stranger is cooing at her baby._

 _I don't think I've ever smoked a joint so quickly in my life. They must not have had a smoke alarm in there, and I sincerely hope that they've since rectified that. After we flushed the roach, we ran out and made our way as quickly as we could to the other side of the aquarium, just trying to put some distance between ourselves and the scene of the crime. As we did, we passed the woman with the baby, and overheard her telling a security guard that someone was smoking in the bathroom._

 _Somewhere along the way, we lost our worksheets, and we spent the rest of the trip choosing our favorite fish in each exhibit and giving them ridiculous names. We made it to the dolphin show on time, and our teacher didn't even mind giving us new worksheets, which we hastily completed during the show._

 _And that was it. We should have been expelled for doing something so stupid. I have absolutely no idea how we managed to get away with it._

 _-...-...-...-...-...-_

"You're completely mental. You know that, right?"

"Indubitably."

"I did go to the aquarium. Twice actually. And you're right. I hated that city, but the aquarium was tops. Do you remember any of the fishy names?"

Red tilted his head and laughed. "Miraculously, yes, a few. The littlest sea horse was Astrid. The stingray with spots was Mary Jane. There was Julio, a sea turtle, and Amelie, a nurse shark. That's all I recall, but there must have been at least a dozen."

"Let me show you how you look when you smoke." Liz plucked the cigar from his fingers and did a laughably exaggerated impression, leaning back in the seat and pursing her lips as she took a deep drag, careful not to inhale or cough. With her eyes closed, she tipped her head all the way back to blow a plume of smoke into the air. As she lifted her head, she languidly moistened her lips and swung her gaze towards Red, smirking at him with hooded eyes.

"Just like that, huh?"

"Exactly like that."

"Hm. No wonder you like it so much. I'm obviously hot. Feel free to hang on to that, if you wish. I also like to watch."

"So you've said."

"Another, then?"

"Yes! Another _!"_

 _-...-...-...-...-...-_

 _Let's see... In tenth grade, the members of the National Honors Society got to take a trip to Harvard's natural history museum. It was kind of a big deal. We took a charter bus, and they played a couple movies to entertain us on the road. I don't recall which ones, because as you may have already guessed, I wasn't watching._

 _I had the good fortune of having a girlfriend who was at least as smart as myself, so she was also a member. Her name was Gillian Bloom. She was one of those stereotypically beautiful little-miss-perfects. Daddy's girl. Teacher's pet. A schedule so jam-packed with extracurricular activities that her only free time was spent sleeping. Except... that wasn't quite true, because like so many perfect girls, she'd also made an art out of determining when she could get away with skipping an obligation in favor of doing something that truly made her happy._

 _For the three months that we dated, I was her 'something'._

 _On the drive to Boston, chaperones were placed at both the front and the center of the bus. Gillie and I got stuck directly behind the one in the center. We were all snuggled up beneath a blanket, holding hands, and the moment that she turned her head to give me a kiss, the chaperone turned around and saw her do it. We received a firm lecture that was absurdly harsh for such a minor offense._

 _That really should have been the end of that, but nope. Minutes later, Gillie turned to me and raised her eyebrows mischievously. Without a word, she hiked up her skirt and put my hand where she wanted it. She wasn't even wearing panties. God, I thought I was going to die._

 _Then she unzipped my fly and... well, you can guess what happened next._

 _While all of that was going on beneath the blanket, we were biting our lips and struggling to keep quiet. Mere seconds away from the point of no return, the chaperone turned around again. We just froze, terrified. My head instantly filled with thoughts of her dad chasing me with a baseball bat._

 _But the chaperone just said, "We should be there in about an hour. Are you guys excited?"_

 _Gillie replied, "Oh yes, very much so."_

 _Hey, it wasn't a lie._

-...-...-...-...-...-

"Oh my god, that's hilarious! Did you at least get to finish?"

"Less than a minute after the chaperone turned around again."

Liz laughed. "Why am I not surprised?"

"Because I was fifteen?"

"Yeah, probably. Sounds messy though. I hope you washed the blanket."

"No idea. It was Gillie's."

"It's a little funny to hear that you were in the NHS. I know that you were smart enough, and I know that your grades were good enough, but the NHS strikes me as something that you'd consider an exercise of tedium. It's hard for me to imagine you toeing such a line."

"I've toed all kinds of lines, love."

She lifted a hand to idly stroke the back of Red's head, relishing in the way he leaned into her touch. "One more, pretty please?"

"Alright, but this is the last one for tonight."

-...-...-...-...-...-...-

 _This one happened somewhere near the end of senior year, when everyone was miles beyond giving a damn about school. It was one of those beautiful days that makes any place with a roof feel like a jail cell. A few of my friends decided to skip school to get drunk and go swimming in the river, but much to my chagrin, I had a huge government test in seventh period._

 _By the time second period rolled around, I had decided to join my friends and try to make it back in time to take the test. When the next bell rang, I took off with my girlfriend, Stephanie Montgomery._

 _Nobody brought a swimsuit, so we all just skinnydipped. Now, if you're imagining some kind of wild drunken river orgy, then stop now, because that didn't happen. We did, however, have a really cool rope swing. To my drunken eye, the girls were absolutely stunning while flying through the air. Graceful, really, like nude Cirque du Soliel acrobats. But the guys? Blech. Dicks and beer bellies flopping around all willy-nilly, like watching a thrown water balloon in slow-mo._

 _Time got away from me. With only thirty minutes left before my test, I was stumbling around on the riverbank in search of my clothes. With a little help from my sympathetic friends, I located everything except for my shirt. Oddly enough, I had completely undressed in one spot, and no one could figure out why or how my shirt had vanished without a trace. My best guess is that it was a prank, but as for who, why, or how, I'll never know._

 _At that point, I started to panic, so I asked everyone to check in their cars to see if they had a shirt that I could borrow. Only one person did._

 _My girlfriend, Stephanie._

 _It was a women's size small, and it looked absolutely ridiculous on me. The short length hit right at my navel, and the armholes interfered with my blood circulation. On me, it was a belly shirt. My options were to either suffer though wearing it at school, or skip the rest of the day and fail the test._

 _I was too drunk to drive, so Stephanie brought me back to school, and just in time, too. I decided to wear that tiny scrap of fabric, but it didn't turn out as humiliating as I had expected. Everyone thought I was just goofing off, fishing for a little shock and awe, and yes, I succeeded in that endeavor._

 _But I also aced the test. How? I'll never know._

-...-...-...-...-...-

"Thanks. That naked-dudes-on-a-rope-swing thing is now permanently burned into my mind."

"Sorry about that," Red replied with a laugh, but he didn't sound sorry at all.

"I think I'm ready to go back inside now, if it's alright."

"I'd never turn down an invitation to go to bed with you."


End file.
